The syntheses of nonnucleoside, HIV-1 reverse transcriptase inhibitors containing a CF2 group

Five‐Membered Heterocycles: 1,3‐Azoles

“…A procedure strictly related to the previous method is the reaction of N-acyl derivatives of 244-246, which undergo thermal dehydration to afford the corresponding benzoazoles (Scheme 10.140) [407][408][409][410].…”

Fluoride-induced nucleophilic (phenylthio)difluoromethylation of carbonyl compounds with [difluoro(phenylthio)methyl]trimethylsilane (TMS–CF2SPh)

“…Column chromatography was carried out using silica gel (60-200 mesh). 1 H, 13 C, 19 F NMR spectra were recorded on Bruker AMX 500 and Varian Mercury-400 NMR spectrometers. (CH 3 ) 4 Si (TMS) was used as an internal standard for 1 H and 13 C NMR, CFCl 3 was used as internal standard for 19 F NMR.…”

“…Recently, the selective introduction of difluoro(arylthio)-methyl or difluoro(heteroarylthio)methyl group (ArSCF 2 ) into organic molecules has been found to be attractive, since these compounds have potential biological applications such as anti-HIV-1 reverse transcriptase inhibitors and other agrochemical intermediates [1,2]. The currently known methods to construct the ArSCF 2 moiety are based on the S R N1 reactions between an aryl-or heteroarylthiolate (ArSNa) and a halodifluoromethyl-containing compound (halo = Br, Cl) [1,2].…”

“…The currently known methods to construct the ArSCF 2 moiety are based on the S R N1 reactions between an aryl-or heteroarylthiolate (ArSNa) and a halodifluoromethyl-containing compound (halo = Br, Cl) [1,2]. To our best knowledge, there is no synthetic method available so far for the direct introduction of a difluoro(arylthio)methyl (ArSCF 2 ) building block into organic molecules.…”

Addition of α,α-Difluoroiodomethylcyclohexyl Ketone to Alkenes under Copper Catalyst

“…anticancer, 5 anti-HIV, 6 and antihypertensive 7 effects. Introduction of difluoromethylene group into organics has been generally accomplished by following methods: the addition of perfluoroalkyl iodide to alkenes in the presence of various catalysts such as titanium, 8 benzoylperoxide, 9 sodium dithionite, 10 and organophosphines; 11 the addition of ethyl bromodifluoroacetate to alkenes using nickel chloride 12 or copper powder 13 as a catalyst; and the transformation of carbonyl group to difluoromethylene group utilizing DAST [(diethylamino)sulfur trifluride].…”